These interviews are republished in their entirety, so there is a bit of repetition on topics and themes. As the interviews take place over many years, you can also see the evolution of David Foster Wallaces' thoughts which makes Conversations with David Foster Wallace well worth the read.

It is difficult to find a conversation with David Foster Wallace that does not have insightful moments. I've marked so many pages I don't know where to start.

Here are some of my notes.

When you write fiction …

“When you write fiction,” he explains as part of his critique of a story about a young girl, her uncle, and the evil eye, “you are telling a lie. It’s a game, but you must get the facts straight. The reader doesn’t want to be reminded that it’s a lie. It must be convincing, or the story will never take off in the reader’s mind.”

When asked ‘What would you like your writing to do,' Wallace gave an honest answer.

It’s very hard to separate what you want the writing to do from your own desires about how you will be regarded because of the work. … So no feelings about desired effect are pure, free of selfish ends.

But there are a few books I have read that I’ve never been the same after, and I think all good writing somehow addresses the concern of and acts as an anodyne against loneliness. We’re all terribly, terribly lonely. And there’s a way, at least in prose fiction, that can allow you to be intimate with the world and with a mind and with characters that you just can’t be in the real world. I don’t know what you’re thinking. I don’t know that much about you as I don’t know that much about my parents or my lover or my sister, but a piece of fiction that’s really true allows you to be intimate with … I don’t want to say people, but it allows you to be intimate with a world that resembles our own in enough emotional particulars so that the way different things must feel is carried out with us into the real world. I think what I would like my stuff to do is make people less lonely. Or really to affect people. … You can’t make sure that everybody’s going to like you, but damn it, if you’ve got some skill you can make sure that people don’t ignore you.

A really great piece of fiction.

A really great piece of fiction for me may or may not take me away and make me forget that I’m sitting in a chair. There’s real commercial stuff can do that, and a riveting plot can do that, but it doesn’t make me feel less lonely.

There’s a kind of Ah-ha! Somebody at least for a moment feels about something or sees something the way that I do. It doesn’t happen all the time. It’s these brief flashes or flames, but I get that sometimes. I feel unalone— intellectually, emotionally, spiritually. I feel human and unalone and that I’m in a deep, significant conversation with another consciousness in fiction and poetry in a way that I don’t with other art.

Echoing comments made by Patagonia founder Yvon Chouinard, Wallace believed in taking joy in the process.

There is a lopsided emphasis in writing programs on hermetic fiction, the mechanicalness of craft, technique, and point of view, as opposed to the more occult or spiritual side of writing— taking joys in the process of creation.

A generation that inherited nothing as far as meaningful moral values.

MTV is just hypnotic. So you’ve got us kids, twenty to thirty-five, right on the edge, and all the kids coming after us really getting sucked into that stuff, but learning it in a way that doesn’t allow any sort of incredulity at all. … This is a generation that has an inheritance of absolutely nothing as far as meaningful moral values, and it’s our job to make them up, and we’re not doing it. And we’re being told, by the very systems that the Sixties were so right to fear, that we needn’t worry about making up moral systems: you know, that there isn’t more to being alive than being pretty, having intercourse a lot, and having a lot of possessions.

For Wallace, writing fiction was an escape to a world where time didn't exist.

“Writing fiction takes me out of time. I sit down and the clock will not exist for me for a few hours. That’s probably as close to immortal as we’ll ever get.”

On learning from an unhappy experience in graduate school.

I didn’t have a very happy experience in graduate school, but it seems there are different ways to learn from it. You can either learn by aligning yourself with the sort of company line at a program or you can play James Dean and align yourself against it. Sometimes it’s not until you have professors— you know, authority figures— kicking your ass, and you still find yourself resisting what they’re saying that you find out what you believe.

What fiction and poetry are doing is what they’ve been trying to do for two thousand years:

affect somebody, make somebody feel a certain way, allow them to enter into relationships with ideas and with characters that are not permitted within the cinctures of the ordinary verbal intercourse we’re having here, you know: you don’t see me, I don’t see you. But every two or three generations the world gets vastly different, and the context in which you have to learn how to be a human being, or to have good relationships, or decide whether or not there is a God, or decide whether there’s such a thing as love, and whether it’s redemptive, become vastly different. And the structures with which you can communicate those dilemmas or have characters struggle with them seem to become appropriate and then inappropriate again and so on.

Responding to a question about how fiction has changed, Wallace pierces deep inside of pop culture.

[O]ne of the ways that things have changed is that fiction used to be a kind of travelogue. It used to be a way to take people to foreign lands and exotic cultures, or to important people, and give readers access to worlds they didn’t have access to. The world that we live in is very different. I can get up and watch satellite footage of a riot in Peking while I eat a Tex-Mex breakfast while I listen to Third World music on my CD player. Fiction’s job used to be to make the strange familiar, to take you somewhere and let you feel that this was familiar to you. It seems that one of the things about living now is that everything presents itself as familiar, so one of the things the artist has to do now is take a lot of this familiarity and remind people that it’s strange.

And taking the familiar and reminding people that it is strange is what he tried to do when he pointed to passive entertainment (see Infinite Jest).

U.S. viewers’ relationship with TV is essentially puerile and dependent, as are all relationships based on seduction. This is hardly news. But what’s seldom acknowledged is how complex and ingenious TV’s seductions are. It’s seldom acknowledged that viewers’ relationship with TV is, albeit debased, intricate and profound. It’s easy for older writers just to bitch about TV’s hegemony over the U.S. art market, to say the world’s gone to hell in a basket and shrug and have done with it. But I think younger writers owe themselves a richer account of just why TV’s become such a dominating force on people’s consciousness, if only because we under like forty have spent our whole conscious lives being part of TV’s audience.

I had a teacher I liked who used to say good fiction’s job was to comfort the disturbed and disturb the comfortable. … Since an ineluctable part of being a human self is suffering, part of what we humans come to art for is an experience of suffering, necessarily a vicarious experience, more like a sort of generalization of suffering. … But now realize that TV and popular film and most kinds of “low” art— which just means art whose primary aim is to make money— is lucrative precisely because it recognizes that audiences prefer 100 percent pleasure to the reality that tends to be 49 percent pleasure and 51 percent pain. Whereas “serious” art, which is not primarily about getting money out of you, is more apt to make you uncomfortable, or to force you to work hard to access its pleasures, the same way that in real life true pleasure is usually a by-product of hard work and discomfort. … The problem isn’t that today’s readership is dumb, I don’t think. Just that TV and the commercial-art culture’s trained it to be sort of lazy and childish in its expectations. But it makes trying to engage today’s readers both imaginatively and intellectually unprecedentedly hard.

it’s too simple to just wring your hands and claim TV’s ruined readers. Because the U.S.’ s television culture didn’t come out of a vacuum. What TV is extremely good at— and realize that this is all it does— is discerning what large numbers of people think they want, and supplying it.

Are there any writers that really knock you out?

I’m a huge Don DeLillo fan, although I think his latest book is one of his worst. The DeLillo of Americana and End Zone and Great Jones Street, The Names, and Libra I love. Maybe Gravity’s Rainbow is a better book, but I can’t think of anybody in this tradition since Nabokov who’s put out a better corpus of work than DeLillo. I like Bellow, and I really like the early John Updike— The Poorhouse Fair, Of the Farm, The Centaur, just in terms of sheer fucking beautiful writing. There are a lot of the Latinists too: Julio Cortázar, Manuel Puig, both recently dead. There are young writers now I was telling you about, like Mark Leyner; William T. Vollman, who’s got four books coming out this year; Jon Franzen, Susan Daitch, Amy Homes. The best book I’ve read recently is by Paul Auster’s wife, who’s named Siri Hustvedt. She’s a Norwegian from Minnesota, who wrote this book called The Blindfold. It’s not a lot of fun, but God is it smart. It’s the best piece of feminist postmodernism I’ve ever read. It makes Kathy Acker look sick because it’s so well crafted. I’m not sure there are any really towering giants. I think some Pynchon, some Bellow, some Ozick will be read a hundred years from now; I think DeLillo, maybe.

Wallace was clearly not a fan of the Brat Pack. Commenting on Bret Easton Ellis' American Psycho, he says:

Look, if the contemporary condition is hopelessly shitty, insipid, materialistic, emotionally retarded, sadomasochistic and stupid, then I (or any writer) can get away with slapping together stories with characters who are stupid, vapid, emotionally retarded, which is easy, because these sorts of characters require no development. With descriptions that are simply lists of brand-name consumer products. Where stupid people say insipid stuff to each other. If what’s always distinguished bad writing— flat characters, a narrative world that’s clichéd and not recognizably human, etc.— is also a description of today’s world, then bad writing becomes an ingenious mimesis of a bad world. If readers simply believe the world is stupid and shallow and mean, then Ellis can write a mean shallow stupid novel that becomes a mordant deadpan commentary on the badness of everything.

Look man, we’d probably most of us agree that these are dark times, and stupid ones, but do we need fiction that does nothing but dramatize how dark and stupid everything is? In dark times, the definition of good art would seem to be art that locates and applies CPR to those elements of what’s human and magical that still live and glow despite the times’ darkness.

And to give DFW the last word.

The reader walks away from real art heavier than she came to it. Fuller. All the attention and engagement and work you need to get from the reader can’t be for your benefit; it’s got to be for hers. What’s poisonous about the cultural environment today is that it makes this so scary to try to carry out. Really good work probably comes out of a willingness to disclose yourself, open yourself up in spiritual and emotional ways that risk making you look banal or melodramatic or naive or unhip or sappy, and to ask the reader really to feel something. To be willing to sort of die in order to move the reader, somehow.